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Segment Reporting - Summary of Gross and Net Written and Earned Premiums, Underwriting Results, Ratios and Reserves for Each of Company's Business Segments (Details) - USD ($)
$ in Millions
3 Months Ended
Mar. 31, 2019
Mar. 31, 2018
Dec. 31, 2018
Dec. 31, 2017
Underwriting Revenues        
Gross written premiums $ 1,013.8 $ 1,116.8    
Net written premiums 617.6 635.5    
Gross earned premiums 817.0 842.6    
Net earned premiums 510.6 533.5    
Underwriting Expenses        
Losses and loss adjustment expenses 311.8 310.2    
Amortization of deferred policy acquisition costs 88.2 90.8    
General and administrative expenses 86.2 95.2    
Underwriting income 24.4 37.3    
Corporate expenses (11.9) (13.7)    
Non-operating income (expense) (39.2) (12.1)    
Net investment income 51.5 47.3    
Realized and unrealized investment gains 42.0 100.6    
Realized and unrealized investment losses (6.2) (138.3)    
Change in fair value of loan notes issued by variable interest entities (1.5) 1.0    
Change in fair value of derivatives (53.3) 23.5    
Interest expense on long term debt (5.5) (7.4)    
Net realized and unrealized foreign exchange gains 5.1 (4.7)    
Other income 1.7 2.1    
Other expenses (0.9) (1.2)    
Income from operations before income tax 6.2 34.4    
Net reserves for loss and loss adjustment expenses $ 4,877.4 $ 5,068.1 $ 4,996.6 $ 5,234.3
Ratios        
Loss ratio 61.10% 58.10%    
Policy acquisition expense ratio 17.30% 17.00%    
General and administrative expense ratio 26.90% 22.70%    
Expense ratio 44.20% 39.70%    
Combined ratio 105.30% 97.80%    
Non-operating expenses related to Effectiveness and Efficiency Program $ 6.1 $ 11.8    
Non-operating expenses related to Merger Agreement 29.8      
Reinsurance        
Underwriting Revenues        
Gross written premiums 538.4 623.5    
Net written premiums 395.6 425.0    
Gross earned premiums 336.5 375.0    
Net earned premiums 276.9 282.5    
Underwriting Expenses        
Losses and loss adjustment expenses 165.8 166.9    
Amortization of deferred policy acquisition costs 62.6 55.9    
General and administrative expenses 27.2 31.6    
Underwriting income 21.3 28.1    
Net reserves for loss and loss adjustment expenses $ 2,871.5 $ 2,823.6    
Ratios        
Loss ratio 59.90% 59.10%    
Policy acquisition expense ratio 22.60% 19.80%    
General and administrative expense ratio 9.80% 11.20%    
Expense ratio 32.40% 31.00%    
Combined ratio 92.30% 90.10%    
Insurance        
Underwriting Revenues        
Gross written premiums $ 475.4 $ 493.3    
Net written premiums 222.0 210.5    
Gross earned premiums 480.5 467.6    
Net earned premiums 233.7 251.0    
Underwriting Expenses        
Losses and loss adjustment expenses 146.0 143.3    
Amortization of deferred policy acquisition costs 25.6 34.9    
General and administrative expenses 59.0 63.6    
Underwriting income 3.1 9.2    
Net reserves for loss and loss adjustment expenses $ 2,005.9 $ 2,244.5    
Ratios        
Loss ratio 62.50% 57.10%    
Policy acquisition expense ratio 11.00% 13.90%    
General and administrative expense ratio 25.20% 25.30%    
Expense ratio 36.20% 39.20%    
Combined ratio 98.70% 96.30%